3-Hydroxybenzyl alcohol → (3-((5-(Trifluoromethyl)pyridin-2-yl)oxy)phenyl)methanol

HRID 1666322Notes

Reaction equation

[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6](Cl)=[N:7][CH:8]=1.[OH:12][C:13]1[CH:14]=[C:15]([CH2:19][OH:20])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6]([O:12][C:13]2[CH:14]=[C:15]([CH2:19][OH:20])[CH:16]=[CH:17][CH:18]=2)=[N:7][CH:8]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 5-trifluoromethyl-2-chloro-pyridine (150.0 g, 0.826 mol) in DMF (1.9 L) was added 3-hydroxy-phenyl-methanol (112.5 g, 0.906 mol) and of potassium carbonate (171.0 g, 1.237 mol). The solids were washed into the flask with 100 mL of DMF. The stirred mixture was heated to 95-105° C. for 5 h. It was cooled to ambient temperature and then poured into 5 L of stirred ice-water. The mixture was extracted with ether:hexane (2:1, 1.5 L, 1.0 L). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo to dryness to give the product (222.5 g, 100%).

Workup

washThe solids were washed into the flask with 100 mL of DMF
temperatureIt was cooled to ambient temperature
additionpoured into 5 L of stirred ice-water
extractionThe mixture was extracted with ether:hexane (2:1, 1.5 L, 1.0 L)
dry with materialThe combined organic layers were dried over magnesium sulfate
concentrationconcentrated in vacuo to dryness

Sources & evidence

ORD record: ord-c2317ef895c3427ebc33456b8307f0a1
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

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